65,010

Monroe County, FL Homes

Section Image Section Image
  • /70

    $2,800,000

    • 4 Beds
    • 3 Baths
    • 3,286 Sq Ft

    21640 Overseas Hwy, Summerland Key, FL 33042

    SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (855) 799-5158

    21640 Overseas Hwy, Summerland Key, FL 33042
  • /22

    $6,500

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • House for Rent

    816 Center St, Key West, FL 33040

    Historic Bahama Conch Home for rent during the off season. It's in the center of Old Town , walking distance to everything and I provide 4 bikes to use included in the rent. Two bedrooms, 1 with a king size bed , 1 with a queen size bed. Full Kitchen, and large bathroom with the original claw foot tub and shower and 1 outdoor private shower. Large backyard for eating or relaxing. A Hammock

    816 Center St, Key West, FL 33040
  • /45

    $1,550,000

    Sold Jan 30, 2026

    28538 John Silver Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $1,242/SF
    • 164 Days On Market

    Current Estimated Value $1,521,588

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    28538 John Silver Rd, Summerland Key, FL 33042
    • /62

      Est $2,531,865

      Not Listed For Sale

      130 Harbor Dr, Tavernier, FL 33070

      • 3 Beds
      • 2 Baths
      • 2,109 Sq Ft
      • Built 2012
      130 Harbor Dr, Tavernier, FL 33070

      Last Sold Summary

      • 6 Days On Market

  • /49

    $1,499,000

    Pending
    • 4 Beds
    • 4 Baths
    • 3,298 Sq Ft

    132 N Indies Dr, Marathon, FL 33050

    Experience the best of the Florida Keys in this beautifully designed 4-bedroom, 4-bath home in the sought-after Duck Key community. This waterfront property boasts an open floor plan, seamlessly blending indoor and outdoor living. The spacious kitchen features ample counter space, perfect for entertaining. Enjoy breathtaking canal views from the covered balcony, or step outside to your private

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    (786) 981-5471

    132 N Indies Dr, Marathon, FL 33050
  • /11

    $3,500

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 780 Sq Ft
    • Townhouse for Rent

    30 Merganser Ln, Key West, FL 33040

    Yearly rental. Fully furnished charming well maintained 2b/1.5b townhome in the Key West golf club. Central AC, Propane Gas stove top and outside grill. 3 Flat screen TVs. Impact windows. Screened in back porch. Paved back yard. Patio furniture. Outside storage. Two community pools, one resort like, and gym facility. Gated entry. Surface parking in front of unit. Smoke free unit. No pets.No drugs.

    30 Merganser Ln, Key West, FL 33040
  • /56

    $880,000

    Sold Apr 15, 2026

    82260 Overseas Hwy, Islamorada, FL 33036

    • 3 Beds
    • 3 Baths
    • 2,314 Sq Ft
    • Built 1964

    Last Sold Summary

    • 22% Below List Price
    • $380/SF
    • 276 Days On Market

    Current Estimated Value $955,474

    Last Listing Agent The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    82260 Overseas Hwy, Islamorada, FL 33036
    • /2

      Est $1,703,953

      Not Listed For Sale

      40 Sunset Key Dr, Key West, FL 33040

      • Studio
      40 Sunset Key Dr, Key West, FL 33040

  • /66

    $4,445,000

    $250K PRICE DROP
    • 8 Beds
    • 4 Baths
    • 4,681 Sq Ft

    136 San Remo Dr, Islamorada, FL 33036

    Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique

    Agent Photo

    Shane Wilson

    Cypress Realty, Inc.

    (645) 215-8760

    136 San Remo Dr, Islamorada, FL 33036
  • /8

    $1,975

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 905 Sq Ft
    • House for Rent

    354 Oleander Dr, Tavernier, FL 33070

    Just renovated in Tavernier. Seperate Laundry room. First and security. No smoking, no pets.

    354 Oleander Dr, Tavernier, FL 33070
  • /6

    $2,200

    Sold May 15, 2026

    91865 Overseas Hwy Unit 106, Tavernier, FL 33070

    • 1 Bed
    • 1 Bath

    Last Sold Summary

    • 8% Below List Price
    • 6 Days On Market

    Last Listing Agent Kevin Cornell Cornell Commercial Real Estate, Inc.

    91865 Overseas Hwy Unit 106, Tavernier, FL 33070
    • /81

      Est $2,935,656

      Not Listed For Sale

      Unlisted Address

      • 4 Beds
      • 3.5 Baths
      • 2,662 Sq Ft
      • Built 2015
      Unlisted Address

      Last Sold Summary

      • 42 Days On Market

  • /69

    $3,400,000

    Open Sat 11AM - 2PM $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-0155

    1083 Labat Ln, Cudjoe Key, FL 33042
  • /13

    $3,550

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • Condo for Rent

    3312 Northside Dr Unit 111, Key West, FL 33040

    Available NOW through January 30,2027!Welcome to paradise in Santa Clara Condominiums — a beautifully renovated, fully furnished 2 Fully renovated kitchen & bathroomsHurricane-impact windows & doorsSpacious walk-in storage/closet spacePrivate patio & secluded yard areaDirect access to tennis courts & poolOn-site laundry & secure entryJust minutes from beaches,

    3312 Northside Dr Unit 111, Key West, FL 33040
  • /44

    $630,000

    Sold Jun 16, 2025

    130 Ocean View Dr, Tavernier, FL 33070

    • 3 Beds
    • 1 Bath
    • 1,312 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $480/SF
    • 158 Days On Market

    Current Estimated Value $686,901

    Last Listing Agent Taylor Engel Coldwell Banker Schmitt R.E.

    130 Ocean View Dr, Tavernier, FL 33070
    • /5

      Not Listed For Sale

      91655 Overseas Hwy, Tavernier, FL 33070

      • Built 1976
      91655 Overseas Hwy, Tavernier, FL 33070

      Last Sold Summary

      • 40 Days On Market

  • /27

    $987,500

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft

    3962 No Name Rd, Big Pine Key, FL 33043

    Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    (888) 275-1086

    3962 No Name Rd, Big Pine Key, FL 33043
  • /12

    $4,500

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    1113 Grinnell St, Key West, FL 33040

    Fully furnished - beautifully painted in Keyzie colors, 1br/1ba rear cottage in the historic district of Old Town, Key West; 5 blocks to the beach and 4 blocks to the world famous Duval Street with shops, art galleries, restaurants, bars and night clubs.FEATURES:One off street parking spot is included on sitePrivate porch, as well as the use of the fully fenced courtyard and high

    1113 Grinnell St, Key West, FL 33040
  • /26

    $295,000

    Sold Jan 08, 2026

    6099 Overseas Hwy Unit 13E, Marathon, FL 33050

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Built 1976

    Last Sold Summary

    • 15% Below List Price
    • $454/SF
    • 90 Days On Market

    Last Listing Agent Casey Elliott Key Colony Beach Realty

    6099 Overseas Hwy Unit 13E, Marathon, FL 33050
    • /2

      Est $1,055,382

      Not Listed For Sale

      182 Airstream Ln, Tavernier, FL 33070

      • 3 Beds
      • 2 Baths
      • 1,055 Sq Ft
      • Built 1992
      182 Airstream Ln, Tavernier, FL 33070

  • /41

    $62,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    617 Front St Unit A-52 Penthouse Week, Key West, FL 33040

    Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events.

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 215-8159

    617 Front St Unit A-52 Penthouse Week, Key West, FL 33040
  • /34

    $2,950

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    818 White St Unit 5, Key West, FL 33040

    Specials: Get 5% off for a month stay or a deep discount for 6-month bookings in 2026! Available May till October 2026Refundable Security Deposit: $1200.00 (Note: First month's rent, security deposit, and last month's rent are due upfront for long-term rentals.)Additional Features: pool access, porches, private entrance Rebuilt in 2005, this unique home offers modern

    818 White St Unit 5, Key West, FL 33040
  • /12

    $1,050,000

    Sold Mar 03, 2026

    619 Front St Unit 21, Key West, FL 33040

    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • 86 Days On Market

    Last Listing Agent Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

    619 Front St Unit 21, Key West, FL 33040
    • /25

      Not Listed For Sale

      209 Camelot Dr, Tavernier, FL 33070

      • 3 Beds
      • 2 Baths
      • 1,185 Sq Ft
      • Built 1971
      209 Camelot Dr, Tavernier, FL 33070

      Last Sold Summary

      • 45 Days On Market

  • /39

    $1,090,000

    $109K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 920 Sq Ft

    319 Woods Ave, Tavernier, FL 33070

    Charming 2-bedroom, 2-bath ground-level canal-front home located in a highly desirable Florida Keys neighborhood. The home features a split floor plan with a one-bedroom, one-bath layout on one side and a separate efficiency with its own bathroom and private entrance on the other--ideal for guests, extended family, or rental income. This property offers great potential to update and transform

    Agent Photo

    Pierre Bellion

    Ocean Sotheby's International Realty

    (645) 225-2335

    319 Woods Ave, Tavernier, FL 33070
  • /16

    $2,000

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    5D 10th Ave, Stock Island, FL 33040

    Enjoy a private and breezy retreat in this unique one-bedroom, one-bath duplex elevated on stilts in Stock Island. This charming home features a cozy kitchenette and a versatile bonus room that serves perfectly as a home office or an extra-large walk-in closet. Step outside to your private back deck to take in beautiful views, or head down to the backyard for some extra green space. Rent is

    5D 10th Ave, Stock Island, FL 33040
  • /24

    $735,000

    Sold Jul 02, 2025

    19 Whistling Duck Ln, Key West, FL 33040

    • 3 Beds
    • 2.5 Baths
    • 1,060 Sq Ft
    • Built 1995

    Last Sold Summary

    • 18% Below List Price
    • $693/SF
    • 98 Days On Market

    Current Estimated Value $776,026

    Last Listing Agent Kelli Houze Berkshire Hathaway HomeServices Knight & Gardner Realty

    19 Whistling Duck Ln, Key West, FL 33040
    • /32

      Est $394,293

      Not Listed For Sale

      325 Calusa St, Key Largo, FL 33037

      • 2 Beds
      • 2 Baths
      • 300 Sq Ft
      • Built 2018
      325 Calusa St, Key Largo, FL 33037

      Last Sold Summary

      • 147 Days On Market

  • /26

    $419,000

    $170K PRICE INCREASE
    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    105 Avenue D Unit 113, Marathon, FL 33050

    Wake up to gentle canal breezes and end the day with your boat tied just steps from home. This beautifully updated waterfront condominium offers an exceptional Florida Keys lifestyle along a serene 200-foot-wide deep-water canal with 6+ ft control depth and no bridge clearance restrictions, making it ideal for sailboats, sportfish, and cruising vessels. The residence includes an ASSIGNED boat

    Agent Photo

    Natallie Liz

    Expert Realty LLC (HQ)

    (305) 702-1508

    105 Avenue D Unit 113, Marathon, FL 33050
  • /14

    $2,600

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    44 Gumbo Limbo Ave Unit Upstairs, Key Largo, FL 33037

    Beach Cottage Living in Key Largo. Must see, beautiful 2 bed, 2 bath home in a desirable Key Largo neighborhood at MM94. The location is ideal, near Key Largo, Tavernier, and Islamorada. The kitchen has granite counter tops, and bathrooms are beautifully tiled. There is a spacious shaded screened in porch perfect for outdoor furniture and plants. The house is unfurnished and move in ready.

    44 Gumbo Limbo Ave Unit Upstairs, Key Largo, FL 33037
  • /43

    $735,000

    Sold Jan 05, 2026

    1 Orange Dr, Key Largo, FL 33037

    • 4 Beds
    • 3 Baths
    • 1,652 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $445/SF
    • 2 Days On Market

    Last Listing Agent Terry Canto American Caribbean Real Estate, Christie's International Real Estate

    1 Orange Dr, Key Largo, FL 33037
    • /42

      Est $1,487,915

      Not Listed For Sale

      118 S Layton Dr, Long Key, FL 33001

      • 3 Beds
      • 3 Baths
      • 1,560 Sq Ft
      • Built 1981
      118 S Layton Dr, Long Key, FL 33001

      Last Sold Summary

      • 44 Days On Market

  • /61

    $1,449,000

    • 2 Beds
    • 2 Baths
    • 1,372 Sq Ft

    21012 6th Ave, Summerland Key, FL 33042

    Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (645) 666-1284

    21012 6th Ave, Summerland Key, FL 33042
  • /26

    $2,450

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 778 Sq Ft
    • Condo for Rent

    98402 Windward Ave Unit 98402 Windward Ave, Key Largo, FL 33037

    Fabulous PICTURES OF AMENITIES. Landings of Largo offers a resort-like atmosphere for an affordable price. Available July 1st, 2026. Preview now so you don't miss this Garden Apartment. One Year lease with option to renew. View of the Pool from your second floor condo. Nice upgrades, granite counter tops. Gated Community with many great amenities. Tennis courts, boat ramp, sunset pier, 2 pools,

    98402 Windward Ave Unit 98402 Windward Ave, Key Largo, FL 33037
  • /33

    $4,500

    Sold Dec 09, 2025

    155 Long Key Rd, Key Largo, FL 33037

    • 3 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Built 1973

    Last Sold Summary

    • 4% Below List Price
    • $3/SF
    • 113 Days On Market

    Last Listing Agent isabel linowitz RE/MAX All Keys Real Estate

    155 Long Key Rd, Key Largo, FL 33037
    • /60

      Est $971,592

      Not Listed For Sale

      40 Florida Dr, Key Largo, FL 33037

      • 4 Beds
      • 3 Baths
      • 2,116 Sq Ft
      • Built 2010
      40 Florida Dr, Key Largo, FL 33037

      Last Sold Summary

      • 69 Days On Market

  • /47

    $675,000

    $24K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 780 Sq Ft

    62 Merganser Ln, Key West, FL 33040

    Beautiful Townhome in the Gated Key West Golf Club Community! Welcome to island living in the highly desirable Key West Golf Club community! This charming 2-bedroom, 1.5-bath townhouse is located in one of Key West's most picturesque and peaceful gated neighborhoods. Surrounded by lush tropical landscaping and tree-lined streets, this home offers the perfect blend of relaxation and convenience.

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 220-1230

    62 Merganser Ln, Key West, FL 33040
  • /25

    $1,800

    Total Monthly Price

    • 6 Beds
    • 6.5 Baths
    • 3,840 Sq Ft
    • Townhouse for Rent

    51 Barcelona Dr, Key West, FL 33040

    NEW CONSTRUCTION. This house is set up for primarily single individuals with your own 300+ sq ft Master bedroom and master bathroom, large closet with a 200 sq ft balcony. Second Level has community washer and dryer with a living room/common area. Third Level there is an extremely large kitchen, huge living room with a 30x8 beautiful view balcony. 3rd floor washer and dryer. Appliances are all

    51 Barcelona Dr, Key West, FL 33040
  • /3

    $290,000

    Sold Aug 29, 2025

    351 46th St, Marathon, FL 33050

    • 2 Beds
    • 2 Baths
    • 768 Sq Ft
    • Built 1993

    Last Sold Summary

    • 23% Below List Price
    • $378/SF
    • 413 Days On Market

    Last Listing Agent Bill Wilkinson Key to the Keys Real Estate, Inc

    351 46th St, Marathon, FL 33050
    • /2

      Not Listed For Sale

      808 Oakwood Ave, Key Largo, FL 33037

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1994
      808 Oakwood Ave, Key Largo, FL 33037

Showing Results 161 - 200, Page 5 of 18

How to Buy a Home How to Finance a Home How to Sell a Home